Kendrick Lamar has made history by becoming the most-awarded rapper in Grammy Awards history, with 27 wins. Lamar has surpassed Jay-Z, who has 25 Grammy awards. Lamar, who was nominated in nine categories, has won five awards at the 68th Grammy Awards, including Best Melodic Rap Performance and Record of the Year for 'Luther' and Best Rap Album for 'GNX'.